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Ligand-controlled palladium catalysis enables switch between mono- and di-arylation of primary aromatic amines with 2-halobenzothiazoles

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Abstract

Herein, a wide range of mono- and di-arylated products were efficiently prepared from C–N coupling of 2-halobenzothiazoles and primary aromatic amines, and representative compounds 3b and 4b were further confirmed by X-ray crystallography. It was noteworthy that the di-arylated products, denoted as di(benzothiazolyl)amines, are new chemical entities which have not yet been reported. Moreover, the ligand-controlled protocol was extended to the synthesis of target molecules bearing a diphenyl ether or diphenyl amine scaffold. To our delight, several compounds exhibited good inhibitory activity against succinate-cytochrome c reductase (SCR), which revealed the practical application of this protocol. Notably, selective mono- and di-arylation could be switched simply by varying the ligand from Xantphos to a pyridine-functionalized N-heterocyclic carbene (NHC) ligand, and further investigations were carried out to elucidate the possible reason for this new finding.

Graphical abstract: Ligand-controlled palladium catalysis enables switch between mono- and di-arylation of primary aromatic amines with 2-halobenzothiazoles

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Submitted
23 Mar 2020
Accepted
27 May 2020
First published
28 May 2020

Org. Chem. Front., 2020, Advance Article
Article type
Research Article

Ligand-controlled palladium catalysis enables switch between mono- and di-arylation of primary aromatic amines with 2-halobenzothiazoles

Y. Zhu, R. Zhang, W. Sang, H. Wang, Y. Wu, B. Yu, J. Zhang, H. Cheng and C. Chen, Org. Chem. Front., 2020, Advance Article , DOI: 10.1039/D0QO00361A

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